Acetic Acid → Propionic Acid
Reaction equation
[C:1]([Cl:5])(=[O:4])[CH2:2][CH3:3].C(O)(=[O:8])C>>[C:1]([OH:4])(=[O:8])[CH2:2][CH3:3].[C:1]([Cl:5])(=[O:4])[CH3:2].[C:1]([Cl:5])(=[O:4])[CH2:2][CH3:3]Participants
Procedure
If X is the carboxyl group O—C(O)—R5, carboxylic anhydrides are obtained. If R1 and R5 are each methyl, acetic anhydride is obtained, this being prepared industrially from acetic acid via the dehydration to give the ketene and subsequent addition of acetic acid (Weissermel, Arpe, Industrielle organische Chemie, 3rd edition, VCH, 1988, pages 193-194). Propionic anhydride can be obtained from propionic acid by dewatering, or by reaction with propionyl chloride. Mixed anhydrides in which R5 is not methyl or ethyl can be obtained from acetic acid or propionic acid via acetyl chloride or propionyl chloride with subsequent reaction of the corresponding carboxylic acid (Ullmanns Encyklopädie der technishen Chemie, 4th edition, 1980, Verlag Chemie GmbH, Volume 19, page 457).
Sources & evidence
- ORD record
- ord-5226a0b3a7fc437ba56d8c3ef26cf388
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174921B2
Reaction notes
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